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Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (51 reviews)
"Len provided me with an outdoor table and extra chairs so I could have dinner outside with my family because one had the flu. So wonderful to be able to socialize with everyone without risking getting the flu! House was very comfortable and well supplied. Close to downtown and hiking. Off street parking for one car. Thank you so much!!!"
United States
Judy
The price is CA $149
CA $320 total
includes taxes & fees
Aug 3 - Aug 4
East Main Downtown Bungalow

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is CA $208
CA $340 total
includes taxes & fees
Jul 29 - Jul 30
Hanna's House by WanderLodges

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (66 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
The price is CA $263
CA $471 total
includes taxes & fees
Aug 4 - Aug 5
Courtside Cottage - WalkScore 93 - Dog Friendly

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is CA $323
CA $594 total
includes taxes & fees
Aug 10 - Aug 11
Savage Upon Siskiyou

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (53 reviews)
"The Carriage House was amazing! Better than anticipated. Super close to downtown, beautifully appointed, and priced really well! We only stayed one night while driving from California to northern Oregon but we wished we had planned our trip so we could have stayed longer. We will definitely be back. I highly recommend staying here."
United States
Teresa
The price is CA $210
CA $350 total
includes taxes & fees
Aug 24 - Aug 25
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is CA $211
CA $416 total
includes taxes & fees
Jul 30 - Jul 31
Barclay Klum House by WanderLodges

Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (16 reviews)
"Excellent communication as I asked if we could check in early as I arrived earlier than expected. Room was quiet and comfortable. Understood the street parking so was expecting it. Centrally located to downtown. No issues. Thanks for the stay."
United States
Ralph
Quaint Downtown Ashland Studio- pet friendly!

Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.6 out of 10, Exceptional, (17 reviews)
"very relaxing in a beautiful environment with easy access to the OSF and restaurants "
United States
Larry D.
The price is CA $227
CA $326 total
includes taxes & fees
Jul 29 - Jul 30
Chateau Herbe ~ Oberon Suite w/ Kitchen

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is CA $190
CA $345 total
includes taxes & fees
Aug 4 - Aug 5
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
10.0 out of 10, Exceptional, (27 reviews)
"Our out of town in-laws loved their stay. We highly recommend it!"
United States
Alessandro C.
The price is CA $154
CA $337 total
includes taxes & fees
Aug 12 - Aug 13
The Ashland Social | Guest Studio

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (48 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
The price is CA $244
CA $351 total
includes taxes & fees
Aug 17 - Aug 18
A Cowslip's Belle Inn

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is CA $185
CA $342 total
includes taxes & fees
Aug 9 - Aug 10
Charming carriage house in Ashland near downtown

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is CA $313
CA $554 total
includes taxes & fees
Aug 16 - Aug 17
The Mountain Ave House by WanderLodges

Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.

Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Well stocked and comfortable, we didn’t have time for the hot tub, but the shower was lovely."
United States
ashley b.
The price is CA $194
CA $359 total
includes taxes & fees
Aug 18 - Aug 19
Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.

Hanna`s House | Downtown Retreat, Steps to OSF

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (170 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
The price is CA $216
CA $404 total
includes taxes & fees
Jul 29 - Jul 30
Hanna`s House | Downtown Retreat, Steps to OSF

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Grandview of Ashland was a beautiful home!! It was super clean and the views of the valley were amazing. Our entire party had a wonderful time and would 100% stay there again. Highly recommend!"
United States
Paul
The price is CA $409
CA $700 total
includes taxes & fees
Aug 10 - Aug 11
Grandview of Ashland

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (8 reviews)
"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."
United States
Cameron A.
The price is CA $252
CA $355 total
includes taxes & fees
Jul 29 - Jul 30
Chateau Herb ~ Miranda Carriage House Apt

The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"The sights stunning, the garden a delight & the jacuzzi soak enriched my soul & ailing body"
United States
David B.
The price is CA $262
CA $428 total
includes taxes & fees
Aug 3 - Aug 4
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (231 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is CA $248
CA $421 total
includes taxes & fees
Aug 17 - Aug 18
The Ashland Cottage, walk to town

Swank House -Downtown Suite- Pet Friendly

Swank House -Downtown Suite- Pet Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, cute and private outdoor patio. Cozy but spacious bed and room. Pet-Friendly. Would definitely stay again."
United States
Katie I.
The price is CA $252
CA $325 total
includes taxes & fees
Aug 3 - Aug 4
Swank House -Downtown Suite- Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theater scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly: This highly rated vacation home rental in Ashland offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Gorgeous Lakeside BarnHOUSE + SAUNA! as a favorite home for rent in Ashland.

How many vacation rentals are there in Ashland?

Choose from 105 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Angus Bowmer Theatre and Oregon Shakespeare Festival, whereas Lithia Park and North Mountain Park are a couple of picturesque spots to enjoy the outdoors. Emigrant Lake and Mount Ashland Ski Area are other places to visit while you're in town.

What are vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.